Yu Yi-Han, Sun Gang, Zhao Di, Wu Yi-Kai, Yuan Haoliang, Wen Xiaoan, Liu Liu, Xu Qing-Long
Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases and State Key Laboratory of Natural Medicines, China Pharmaceutical University, 639 Longmian Dadao, Nanjing 211198, China.
J Org Chem. 2024 Aug 16;89(16):11588-11592. doi: 10.1021/acs.joc.4c01276. Epub 2024 Aug 4.
This work reports a method for the catalytic synthesis of C(3) SCF-substituted pyrrolidinindoline using a small-ring organophosphorus-based catalyst and a hydrosilane reductant, with trifluoromethanesulfonyl chloride as the electrophilic SCF reagent. This method can drive the conversion of tryptamine to the C(3) SCF-substituted pyrrolidine indoline. The readily available, inexpensive trifluoromethanesulfonyl chloride could be activated as an electrophilic SCF source by P/P redox catalysis and could efficiently participate in the reaction of tryptamines, thus providing various substituted C(3) SCF-substituted pyrrolidinoindoline in moderate to excellent yields. This presented strategy features a broad substrate scope, and the structure has value for in-depth research.
这项工作报道了一种使用基于小环有机磷的催化剂和硅烷还原剂,以三氟甲磺酰氯作为亲电SCF试剂催化合成C(3) SCF取代的吡咯烷二氢吲哚的方法。该方法可驱动色胺转化为C(3) SCF取代的吡咯烷二氢吲哚。易于获得且价格低廉的三氟甲磺酰氯可通过P/P氧化还原催化被激活为亲电SCF源,并能有效参与色胺的反应,从而以中等至优异的产率提供各种取代的C(3) SCF取代的吡咯烷并二氢吲哚。所提出的策略具有广泛的底物范围,其结构具有深入研究的价值。